Funcationalization Of Pyrene At 2-position By Phospho-Fries Rearrangement

Pyrene is an important member of the polycyclic aromatic hydrocarbon family,the rigidity and large conjugate planarity of pyrene make it an important building block in organic optoelectronic material.The combination of phosphorus atoms with pyrene unit can further regulation the properties of luminescent materials.Therefore,the design and synthesis of pyrene-based phosphorous compounds is expected to obtain new materials with good luminescence properties.From the viewpoint of the electronic structure,the chemistry of pyrene is strongly position-dependent,it is very difficult to functionalize pyrene at the 2-position.In this thesis,a series of(1-hydroxy)-2-pyrenylphosphine derivatives were synthesized from pyrenyl phosphates via Phospho-Fries rearrangement under mild conditions.The pyrenyl phosphate precursors could be easily obtained from the reaction of 1-pyrenol with H-phosphonates or phosphine chlorides.A series of novel phosphorous-containing pyrene fused conjugated compounds 1,3-oxaphospholes which possess strong blue fluorescence and broader conjugate surface were synthesized via intermolecular cyclization of(1-hydroxy)-2-pyrenylphosphines with N-arylimide chlorides.This work lays the foundation for the subsequent derivatization and application research of such compounds.This research provides not only a convenient method for the funcationalization of pyrene at 2-position but also new organophosphorus basedπ-conjugated molecules.